I set up the LaunchPad using my Mac OS X computer running Windows 8.1 under Parallels. When it tried to update the debugger on the first program attempt, it failed and quit seeing the LaunchPad. I worked with TI to get it fixed and it turns out it's quite simple, see this post, you can fix it from the command line in your Windows guest OS:
http://www.chiefdelphi.com/forums/sh...ight=launchpad
One possible way to prevent it in the first place is to hold down the ALT key when selecting that you want your guest OS to use the USB device (LaunchPad) so that Parallels will remember the choice. That may allow it to reconnect to the Windows machine quick enough to not fail in the first place.